


Playdate

by Mayalaen



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - BDSM, Anal Fingering, Anal Sex, Biting, Blow Jobs, Cock Warming, Dirty Talk, Dom Sam Winchester, Dom/sub, Double Penetration, Double Penetration in Two Holes, Fucking, Gift Fic, Incest Kink, M/M, Nipple Play, Painplay, Public Blow Jobs, Rimming, Rough Sex, Semi-Public Sex, Sensory Deprivation, Spanking, Spitroasting, Sub Dean Winchester, Switch Michael, Switching, Threesome, Threesome - M/M/M
Language: English
Status: Completed
Published: 2016-06-18
Updated: 2016-06-18
Packaged: 2018-07-15 17:56:45
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,636
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7232815
Author URL: https://archiveofourown.org/users/Mayalaen/pseuds/Mayalaen
Summary: <blockquote class="userstuff">
              <p>Dean’s restless between hunts, but Sam has a playdate scheduled. Dean has no idea what Sam has planned for his sub.</p>
            </blockquote>





	Playdate

**Author's Note:**

  * For [majesticduxk](https://archiveofourown.org/users/majesticduxk/gifts).



> This was written for majesticduxk's birthday. It's very, very late. Happy VERY belated birthday, Duck :)

Sam loved watching Dean work. He was confident and smart and downright bossy when they were hunting. In fact, Sam had to be careful that he paid attention to the hunt instead of Dean-watching.

"Time to get to work, Sasquatch," Dean said, tossing a shovel at Sam before plopping down next to the headstone.

Sam rolled his eyes, but he also started digging. Because that how their relationship worked best. Dean was in charge on hunts and Sam was in charge the rest of the time.

Hiding his collar allowed Dean to intimidate other doms, and casually letting it slip out as he talked to a sub to put them at ease, which meant Dean could charm anyone into doing anything. There were times Sam was jealous of how easily Dean could fall into his roles. Most of the time, though, he was just heart-stoppingly proud of Dean.

"Hurry it up," Dean said, flicking some dirt at the back of Sam's head, "the grounds keeper is going to sweep the area in about three hours, so we need to dig, burn, fill it in, and get outta here by then."

"Going as fast as I can," Sam said, already working up a sweat as he imagined everything he was going to do to Dean after they were finished.

*

Dean went to his knees immediately after they walked into the motel room. Covered in grave dirt and sweat, sore and tired from dealing with a ghost that decided it didn't want to be salted and burned. They both had bruises, and Dean had a split lip, but he still went to his knees.

Sam started the shower, then stripped, shoving his clothes into the corner of the bathroom. He grabbed Dean's favorite shampoo from his duffel along with the loofah and scented body soap.

"Come," Sam said as he walked by Dean.

Dean followed him, obediently stripping when Sam told him to, then they both stepped into the shower. It was a tight fit. Shitty little motel shower and two grown men didn't equal easy fit, but they made it work. They'd been doing it for years.

"Stinks," Dean said, nose scrunching up as Sam scrubbed the shampoo through Dean's hair.

Sam grinned at the mild protest. He knew how much Dean really liked the stuff even if his brother would never admit it out loud.

Once they were all clean, Sam turned the shower off and wrapped Dean in a towel, briskly drying him off.

"No underwear, black jeans, a white undershirt, your red flannel, socks, and boots," Sam said.

Dean nodded, then headed to the bedroom to get dressed. Sam wiped down the bathroom, putting their dirty clothes into a bag he'd later give to Dean. Dean hated doing laundry, but he did it when Sam told him to.

Sam got dressed himself, choosing blue jeans and a green flannel. Unlike Dean, he wore underwear.

"You hungry for burgers or pancakes?" Sam asked. There was a 24-hour IHOP just a couple miles away from the motel, but the motel had a 24-hour restaurant that served good burgers.

"Pancakes," Dean said.

"Let's go," Sam said, patting Dean's ass on the way out the door.

The place wasn't crowded. It was a little after three in the morning and only five of the booths were occupied. Dean headed for the back of the restaurant, but Sam grabbed him by the shirt and directed him to a table near the front. Dean let out a groan of protest, but didn't fight him on it.

With the flannel left open, Dean's collar was visible, and the sub who waited on them batted his eyelashes at Sam until he realized Dean was his.

"We'll start with a big stack," Dean said. "You want strawberry or blueberry on top?"

Sam shrugged. "You pick." He politely ignored the way the sub shivered when he realized Sam was one of those doms who allowed his sub to make decisions like that. One of the good ones.

Dean smiled. "Cherry topping with as much whipped cream as you can fit on the plate."

"Yes, sir," the server said, nodding at Dean. "Anything else?"

"We'll be here for a while," Sam said, "so we'll just start with the drinks and the pancakes."

"I'll bring it out as soon as I've managed to make a tower out of the whipped cream," the server said, grinning at them before heading for the kitchen.

Sam scooted back, putting some distance between himself and the table, then patted his lap.

Dean's eyes widened. "What did I do?"

"You're not squirming enough on that chair," Sam said.

Dean shifted on the seat. "See? I'm squirming."

Sam ignored the hopeful smile and patted his lap again. Dean sighed, but obediently draped himself over Sam's lap, letting out a little whine when Sam reached around and opened his jeans, pulling them down to just under the curve of his ass.

He was still spanking Dean when the server set their drinks down on the table, and Sam didn't miss the hungry look in the sub's eyes. Sam wished he had room in his life for more subs, especially ones that obviously didn't have what they needed yet. He knew he could take care of the server, but between Dean and the constant hunting, Sam wouldn't do it.

Sam pulled Dean up, letting him slide down to the floor on his knees. Dean's face was bright red, not just from the pain of the spanking, but because it still got to him when Sam pulled him over his lap in public. Sam leaned down and kissed Dean's forehead before pulling the jeans up and fastening them.

Dean got back onto the chair, squirming a little. Sam hadn't given him a severe spanking, Dean's ass only light red, but Sam appreciated the effort. He loved seeing Dean squirm.

By the time they'd made it through two stacks of pancakes, six eggs, and more bacon than Sam cared to admit, they paid up and headed back to the motel where Sam fell asleep with Dean's head on his chest.

*

It had been over a week since their last hunt, and Dean was getting restless. Sam had already spanked him at the side of the road earlier in the day, and he was close to ordering Dean to pull the car over again.

"That was two," Sam said.

Dean didn't snark, didn't complain, and didn't really respond in any way other than his body tensing more. That was a bad sign. Sam needed to do something or they would be late for an appointment Dean didn't even know they had.

"Pull over."

Dean's shoulders tensed even more, but he did as he was told. "I don't even get to the count of three?" he asked, a challenge in his tone of voice.

He got out of the car, and Sam knew the only reason Dean didn't slam the door was because he didn't want to do any damage to his car. Sam slowly got out, counting to ten in his head. He found Dean already draped over the trunk, ass out and his jeans down around his ankles.

Sam dropped to his knees behind Dean and turned Dean around with hands on his hips. Dean didn't have a chance to say anything before Sam was sucking his cock, holding Dean's hips and pushing him back against the side of the car.

"Do I get in trouble for talking right now?" Dean asked, and there wasn't a hint of attitude in his voice.

Sam hummed around Dean's cock, a clear signal Dean could say whatever he wanted to. Within reason.

"Fuck, Sammy, your mouth," Dean sighed. "Should've asked for something earlier. Sorry. I didn't realize I was so uptight."

Sam swayed them back and forth, making Dean's ass slide over the warm metal of the car. Dean moaned, obviously enjoying the involvement of the car. Like their own little threesome.

As Dean got closer, he put his hands on Sam's head, trying to get deeper, but a quick scrape of teeth over Dean's cock had him removing his hands and putting them behind him on the car.

Dean came with a gasp, then pushed back against the car, grinding his ass against the smooth metal. Sam grinned as he pulled back, watching Dean as he wiped the corners of his mouth.

"Pull your jeans up, get in the car, and keep it civil until we get there or I'm using the paddle on you," Sam said, then got into the car.

Dean was very good the rest of the way.

*

Dean always grumbled about enemas, but Sam had insisted. He'd paid for a good motel room. One with a hut tub in the room and two king-sized beds. The room service menu even looked good.

Once he'd cleaned Dean out, he made him stand in the corner naked. Dean didn't question it. He knew full well the attitude earlier in the day and the grumbling over the enema had earned him something.

There was a knock on the door, and Dean stayed still like he'd been told to do countless times before. It was hard for Dean. Ever the protective big brother even though Sam could damn well take care of himself.

Sam opened the door, smiling at their play partner for the night. He held up a finger to his lips, and the man nodded, keeping his mouth shut as he came in and gave Sam a hug.

"Sam?" Dean said, voice a bit nervous.

"I've brought someone here to play with us," Sam said as he picked up a black scarf and walked to Dean. "He's going to stay quiet and you're going to wear this blindfold," he said as he wrapped the material around Dean's head, covering his eyes, securing it with a knot at the back of Dean's head.

"I don't get to see who it is?" Dean asked.

Sam couldn't help but smile. His brother was excited. He could hear it in Dean's voice. It was a fantasy Dean had for years. Anonymously fucked by someone his dom picked while Sam watched. He also wanted Sam to participate, but the thrill came from trusting Sam completely to choose their partner.

"I'm going to let him fuck you," Sam whispered.

Dean shivered. "I can't see," he said, running his fingers over the material.

"Good," Sam said, hands smoothing down Dean's sides as he turned Dean around. "He knows your safewords and signals. We're both going to hurt you, but he has limits I've already told him about."

"Is there anything I can't do besides take off the blindfold?" Dean asked.

"You have no restrictions other than you have to obey me," Sam said.

"Okay, Sammy," Dean said, nodding.

Sam gestured to Michael, letting him know he could come over and touch. The man didn't hesitate, and Dean gasped as another set of hands rested on his shoulders.

Sam knew he couldn't ask just anybody to join them, but Michael was a fellow hunter they'd known for years, among others. Sam was confident Michael was strong enough to give Dean a run for his money if Dean wanted to put up a struggle for fun, and Michael would have no trouble tying Dean up if that's what they decided to do.

Dean didn't try to hide his attraction to Michael or anybody else he was interested in. Sam always encouraged it. He knew Dean was loyal to him and had no doubt in his mind Dean was faithful no matter what. That also meant both of them were completely comfortable bringing in a third person to play with.

Sam was fairly certain Dean didn't know who was in the room with them, and there was a possibility Dean wouldn't figure it out since they'd never spent a lot of time in close quarters with Michael.

"What do I call him?" Dean asked.

"Sir," Sam said, grinning when Dean huffed out a laugh.

"What does Sir want me to-ah! Fuck!" Dean yelped as Michael turned him and slammed him into the wall, Dean's upper back taking the brunt of the hit instead of his head because Michael knew what he was doing.

"Shhh," Michael hissed in Dean's ear, then bit down on Dean's left shoulder.

Dean gasped, wincing at the pain. When Michael pulled back, there was a perfect set of prints on Dean's shoulder from the man's teeth. Sam rubbed a hand over his own crotch, his cock twitching at the way Michael was enthusiastically taking charge. It was just what Sam had hoped for.

Michael wrapped his left hand around Dean's cock and balls, pulling forward even as he wrapped his right hand around the front of Dean's neck and pushed. Dean contorted his body, hips forward to ease the pain in his cock and balls.

"Don't touch," Sam said as Dean's right hand strayed toward Michael's left. "Be a good boy."

Dean bit his lip, trying to ignore the pain, but Michael leaned in and licked at Dean's lips, the grip on Dean's cock and balls loosening. Dean relaxed, letting Michael bite at his lips and jaw.

Michael started stroking Dean's cock. A slow, dry drag. Dean groaned, back arching away from the wall in a way that told Sam Michael had started playing with Dean's hole. Just as Dean was really getting into it, almost writhing, Michael pulled away.

Dean caught himself before falling to the floor. "Oh, that's just mean," he grumbled.

Michael sat down on the edge of the bed and crooked his finger at Dean while looking at Sam. Sam got the message and grabbed Dean's shoulders, directing him backward to the bed.

Sam couldn't resist kissing Dean, and he spread Dean's ass for Michael, grinning into the kiss when Dean whimpered. Sam could feel Michael's hair tickling his hands, but even if he hadn't felt that he would know by the noises Dean was making that Michael was eating him out. Dean made the best noises when he was rimmed.

Dean's cock was poking into Sam's leg, hard and probably leaking on Sam's jeans. Sam heard a loud smack, and Dean accidentally bit Sam's lip.

"Sorry, Sam," Dean said, pulling back and cupping Sam's face in apology. "Didn't expect that."

"S'okay," Sam said, licking his sore lip just as Michael smacked Dean's ass again. Harder.

Dean wrapped his arms around Sam, resting his forehead on Sam's chest as Michael smacked first the left cheek, then the right. Back and forth, harder and harder until Dean was gasping and leaning most of his weight against Sam.

The smacking stopped and Sam felt a tap on his left knee. He looked over Dean's shoulder at Michael and saw the man was wrapping his hands around Dean's hips and pulling him down onto his already-slick cock.

Sam lowered Dean, pushing him down when Dean tried to lift off. Dean was the bossy type, and always wanted to lift off and guide a cock in himself even if he was prepared. Sam was having none of it and between he and Michael they got Dean down onto Michael's lap.

Dean leaned back against Michael's front, wincing as he adjusted to the size of the cock inside him. He shifted, then his mouth opened wide as he sat forward.

"Sam!" he said, urgent tone to his voice as he reached back and wrapped a hand around the base of Michael's cock. 

"What's wrong?" Sam asked, ready to lift Dean off if there was a problem.

"He doesn't have a condom on," Dean said, squirming. "He just fucked into me! He doesn't have a fucking condom on!"

"Hey, calm down," Sam said, cupping Dean's face. "Calm down. It's okay. Dean! It's okay! Stop."

Dean took a shuddering breath and settled. "Sorry."

"You think I'd miss something like that?" Sam asked.

Dean blushed, the skin just below the blindfold turning pink. "No."

"He gets tested regularly," Sam said, "and you're the first one he's gone bare with in over three years."

"Oh, sorry," Dean said.

"It's okay," Sam said, then kissed the corner of Dean's mouth.

"S'kinda hot," Dean said, grinning.

Sam chuckled. "Yeah, I thought you'd get a kick out of that."

Michael pushed Dean forward, bending him, then grabbed his hips and pulled him back, giving Dean a clear signal he wanted Dean to fuck himself on Michael's cock.

Dean got the message and started moving. Sam stood back and took his clothes off, watching Dean ride Michael's cock. Michael flopped back onto the bed, letting Dean do all the work.

Sam pushed Dean back to lie on Michael, then spread their legs, getting down on his knees and licking over the base of Michael's cock, Dean's hole, and sucked on Dean's balls before running back down over his hole and around Michael's cock, then sucking on Michael's balls.

Michael kept moving, fucking up into Dean slowly while Sam licked at them, teasing them both. His rhythm stuttered when Sam pushed a spit slick finger in Michael's hole. He heard a soft chuckle and pushed in deeper, finding Michael's prostate and giving him a little stimulation as he sucked at Dean's hole, tight around Michael's cock.

"Ow, ow, ow, fuck, ow!" Dean whined, squirming.

Sam looked up and chuckled. Michael was pinching both of Dean's nipples, twisting them harshly. Dean's cock twitched, another drip of precome oozing its way onto his stomach.

"Keep moving, Dean," Sam said, smacking Dean's inner thigh.

"Ah, fuck, Sammy!" Dean yelped, closing his legs.

"Fuck yourself on his cock or you'll get more," Sam said, scratching over the pink handprint on Dean's thigh.

Dean planted his feet on the bed again and started moving. Michael twisted his nipples, pulling, and Dean lost his rhythm, so Sam landed a hard smack on the opposite thigh.

"Ah, fuck!" Dean yelled, trying to sit up, but Michael had a good hold on Dean's nipples.

Sam pushed a second finger into Michael's hole and pulled up, smiling when Michael gasped, ass grinding down on Sam's fingers. Given the invitation, Sam pushed a third finger in, chuckling as Michael let out a moan. Sam was happy he'd chosen a switch to play with them.

He remembered some of the things Michael had talked about, some of the things that turned him on, and as the two of them moved against each other, Sam leaned in and bit the inside of Michael's left thigh.

"Ah!" Michael screamed.

"Fuck, Sam, I wanna see," Dean said, trying to sit up now that Michael had let go of his nipples. "Please, I wanna see!"

"How about I just do to you what I did to him?" Sam asked, smirking.

"I wasn't asking for-ah! Oh, fuck!" Dean cried out, falling back against Michael as Sam bit into his right thigh. "I don't need to see. I won't ask again. Really."

Sam ran his lips over Dean's opposite thigh, letting his teeth scrape just a little. Dean flinched, breathing a little erratic as he forced himself to stay still.

"Oh, fuck, Sa-Sammy! Oh, fuck that hurts!" Dean growled as Sam made an identical impression on Dean's left thigh.

Just as Sam was about to bite Michael's thigh, giving him a matching set as well, Michael started to move. He flipped them over, covering Dean with his body and fucking into him so hard Dean let out a grunt.

Sam crawled between their legs and pushed his fingers back into Michael's ass, fingerfucking him as Michael fucked Dean. Michael's hole was clenching around him, and it was so warm and tight that the only thing stopping him from shoving his own dick in there was how beautiful the two of them looked on the bed.

Dean's body was flushed and he was sweating, trying to spread his legs wider to accommodate Michael as the man fucked him hard enough that the headboard was hitting the wall. Michael's ass was clenching and releasing as he fucked in and out of Dean, legs straining because he was so close, so fucking close to coming that Sam could feel it in the tension of his body.

Michael gasped, then whimpered as his body locked up, shoving deep inside Dean as he came, asshole spasming around Sam's fingers. He flopped down onto Dean, still slowly fucking in and out, jizz leaking out of Dean's asshole around Michael's cock.

Sam took advantage of the natural lube and pushed a finger in beside Michael's cock.

"Sam!" Dean cried out, unable to move because of the weight on top of him.

Sam found Dean's prostate and stroked it hard, pushing his sub over the edge, body writhing underneath the heavy weight of Michael, sated and warm, draped over Dean.

As soon as Dean stopped squirming and relaxed against the bed, Sam shoved Michael off him and climbed onto the bed, rolling Michael onto his back and pulling his legs apart, sinking into him as Michael looked up at him, eyes wide.

Michael winced, wriggling a little until his body adjusted, then he grinned, putting his legs up on Sam's shoulders. Sam took the hint and started pounding into him.

"Lemme take the blindfold off!" Dean almost yelled as he got to his knees on the bed. "Sam, please! I wanna see! Please! Please!"

Sam chuckled, a drip of sweat falling from the tip of his nose onto Michael's chest. "Think we should indulge him?"

Michael looked over at Dean, who had his fingers already curled around the blindfold, ready to rip it off when given permission. "Sure," he said.

Dean didn't even wait for Sam to say yes. He pulled it off and threw it across the room, eyes going first to Sam, then down to Michael. "Oh, fuck," he groaned, falling back onto his heels. "So fuckin' hot! Fuck. Had no idea it was you."

Michael smirked. "Disappointed?"

Dean snorted. "Fuck, no! Fuckin' wanted to play with you for a long time."

Sam wrapped his left hand around Michael's neck and squeezed. Michael's asshole clenched around him, his body fighting it even if Michael liked breathplay.

"So fuckin' hot," Dean breathed.

Michael coughed and gasped when Sam let go, his right arm going between Dean's legs, two fingers pushing into Dean's asshole.

"Spread out so Sam can see you," Michael said, hooking his fingers inside Dean and pulling him closer.

Dean yelped, but did as he was told, spreading his knees wide and arching his back, planting his hands on the bed for leverage behind him.

"He's a mess," Michael said. "Fucked him open wide and left him wet. Messy hole."

Sam winced, fucking Michael and trying to think of something else so he didn't come yet. He didn't want to. Not yet. It felt too good.

Dean whimpered as Michael fucked in and out of his hole, the squelching sound obnoxious and dirty and so good. He pulled his fingers out and held them up so Sam could see. Wet and dripping. He pushed his fingers into his mouth and sucked loudly, groaning around them.

"Shit," Sam hissed, fucking Michael even harder. 

"Want a taste of your boy?" Michael asked as he held his fingers up, then pushed them into Dean's hole again.

Sam hissed, his balls pulling up. So close. So close he could feel it in his teeth. He opened his mouth as Michael held his messy fingers up, and he sucked on them, moaning.

Just as he was about to come, he pulled out, his jizz painting Michael's stomach and spent dick. Sam groaned as he sat back, holding his cock, stroking slowly as he came down.

"Clean him up," Sam said to Dean.

Dean didn't wait to be told a second time. He leaned forward and licked at Michael's stomach, tip of his tongue following the dribbles. Sam grabbed Dean's hips and pulled him up and over as he shoved his tongue into Dean's wet hole.

Michael chuckled as Dean tried to hang on, still licking at Michael's stomach as Sam sucked on his hole. Finally Sam let go of Dean and flopped onto the bed, grabbing a pillow and shoving it under his head.

"I'll get a towel," Dean said as he started to climb off the bed.

Sam sat up and grabbed his arm, pulling Dean down between them and snuggling up to him. "We'll take a shower in a little while. Right now I just wanna hold you guys."

"We're gonna be all sticky," Dean complained, squirming.

Michael turned onto his side, facing them, and smacked Dean's ass. "Are you giving your dom a hard time?"

Dean scowled at him. "I'm the big brother. I get to do that."

Michael laughed. "Okay, I'll go along with that," he said, then snuggled up to Dean, resting his head on Dean's chest. "Dude, I just banged brothers. First time I've ever scored siblings."

"You told me you fucked twins," Sam said. "You said it was a kink of yours."

"I lied about fucking those chicks because you were freaking out about the whole brother-on-brother thing," Michael said, chuckling.

"Wait, you knew we were brothers back when you said that?" Sam asked.

"Why do you think I said it?!" Michael chuckled again. "You two were fuckin' hot and I wanted to get in on that. The whole hunting buddies line you pulled on me never worked. Not even for a second."

"See, told you he'd be okay with it," Dean mumbled.

Sam sighed. "Yeah, you did."

"So next time we do this," Michael said, sitting up enough that he could look down at both of them, "I wanna hear some dirty talk about it from the both of you. No hiding that shit from me, okay?"

"Next time?" Sam asked just as Dean chuckled and said, "Hell yeah!"

Michael put his head back down on Dean's shoulder. "The two of you are fun and easy to play with. I'm hoping this wasn't a one-time thing."

"We'll play again," Dean said.

"We will?" Sam asked, grinning as Dean elbowed him.

"Yes, we will," Dean said. "He's fun and you enjoyed him as much as I did, so quit being a little bitch."

"Quite a mouth on him, Sam," Michael said. "Should probably plug that with something."

"We could plug both ends," Sam said as he grabbed Dean by the back of the neck and shoved him down over his dick. "Cockwarmer."

"Mmm, sounds nice," Michael said, shifting on the bed.

Sam chuckled as Dean squeaked around his cock, Michael obviously pushing back into him.

"Think you can sleep like that?" Michael asked.

"Me?" Sam asked as he ran his fingers through Dean's hair. "I know I can. Dean, maybe not so much."

"Aww, but wouldn't it be cute if we woke up and he was drooling all over your lap?" Michael asked.

Dean started to lift his head, but Sam pushed him back down.

"Cockwarmers don't talk," Sam scolded, then tapped the end of his nose.

Sam felt a barely-there scrape of teeth and saw the mischief in Dean's eyes. Dean may have been a sub, but Sam never doubted that was a choice on Dean's part, not something he'd been forced into. It part of what made their relationship so perfect. So right.

"Feels good," Michael said as he pulled the blanket over them. "I think I'd like a cockwarmer every night."

Sam chuckled. "Dean's good at fixing people up. Maybe he could help you find your own sub for the times when we can't meet up."

"Mmm, yeah," Michael said, closing his eyes and snuggling in. "Like the sound'a that."

Sam fell asleep with Dean's lips wrapped around his softening cock and Michael's warm breaths puffing against his shoulder.


End file.
